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27 Osborn Road

Sherman, Connecticut 06784

ACTIVE$1,595,000
Beds
4
Baths
3 | 1
SqFt
3,540
Acres
7.71
Year Built
2012
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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About This Home

This impeccable 4 bedroom home is sited on 7.7 private acres w/four fenced paddocks and a 3/4 stall stable for horses at the end of a quiet country lane.The home has a sought after open floor plan on the 1st level. The large, eat-in kitchen has a vast granite center island & includes a 6 burner/two oven range w/egress to the outdoor stone terrace. The open flow to the family room and dining room is ideal for today's lifestyle. The family room features built-ins & an Extraordinaire Fireplace capable of heating the entire home! It is back to back with the outdoor fireplace on the expansive stone terrace. A convenient first floor bedroom with a newly renovated full bath can also be used as a gym, office or library. There is an additional room at that end of the home that is perfect for a home office, den or music room. The upper level has 3 bedrooms including the primary ensuite bedroom w/3 walk-in closets. There is a hall bath for the other two bedrooms to share. The walk-out lower level/basement has high ceilings & a poured concrete foundation. The beautifully appointed 4 stall/3 stalls plus tack room, center aisle stable has large stalls with a stone aisle. The stalls have rubber matting & the 4 fenced paddocks are all adjacent to the barn. There is a fenced round pen as well as access to the Naromi trail system. The in-ground pool is heated and fenced with lovely gardens surrounding it. A charming, in character garage/storage building graces the property as well.

Key Facts

City/Town
Sherman
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
2012
Days on Market
136 days
Beds
4
Baths
3 full · 1 half
Living Area
3,540 sq ft
Lot Size
7.71 acres
Garage / Parking
3 garage
Property Taxes
$9,225 / Annually

Market Snapshot

The Sherman Market

Single Family · trailing 12 months

Median Days on Market

63

28 active listings

Median $ / Sq Ft

$340

28 active listings

Sale-to-List Ratio

96.5%

43 sales

How this home compares

List Price

$1.59M

vs $1.05M median

51.9% above median

Price / Sq Ft

$451

vs $340 median

32.6% above median

Days on Market

136 days

vs 63 days median

73 days longer than median

Based on 28 active and 43 closed sales (trailing 12 mo) of single family in Sherman. Source: SmartMLS · As of July 30, 2026.

Location

27 Osborn Road, Sherman, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$9,433

per month

  • Principal & Interest$8,132
  • Property Taxes$769
  • Insurance$532
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Sherman
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
2012
New Construction
No/Resale
Living Area
3,540 sq ft

Schools

Elementary
Sherman
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hydro Air
Heat Fuel
Propane
Cooling
Central AirZoned
Fireplaces
2
Laundry
Main Level
Laundry Location
Near the mudroom & garage
Appliances
Gas CooktopOven/RangeMicrowaveRefrigeratorFreezerDishwasherWasherDryer
Basement
FullFull With Walk-Out
In-Law Apartment
No
Interior Features
Auto Garage Door OpenerOpen Floor PlanSecurity System
Additional Rooms
FoyerLaundry RoomMusic Room

Exterior & Lot

Lot Size
7.71 acres
Zoning
Residential
Garage / Parking
3 garage spacesAttached GarageDetached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Pool
HeatedSafety FenceSalt WaterIn Ground Pool
Construction
Clapboard
Color
Beige
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
TerraceBarnDeckGarden AreaStablePaddock
Lot Description
Professionally Landscaped

Listing & Financials

Property Taxes
$9,225 / Annually
Days on Market
136
MLS #
24159584
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Sally Slater

(914) 584-0137

Douglas Elliman of Connecticut

(203) 622-4900

Co-Listed By

Robyn Bonder

Douglas Elliman of Connecticut

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/30/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/30/2026 at 7:40 PM UTC.